2-Allyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol → 2-n-Propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol

HRID 2248Notes

Reaction equation

HRID 2248 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:22])[CH:2]=[CH2:3].[H][H]>C(O)C.Cl.[Pd]>[CH2:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:22])[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 189184412-Allyl-4-[4-(4-pyridyl)piperazin-1-yl]phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 189186162-n-Propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenolYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The product from Example 134, step (ii) (0.74 g) in ethanol (25 ml) and 1N hydrochloric acid (2.5 ml) was hydrogenated at room temperature and atmospheric pressure over 10% palladium charcoal (0.15 g) until uptake of hydrogen was complete. Catalyst was removed by filtration through diatomaceous earth and the filtrate evaporated. The residue was triturated with a mixture of ethyl acetate (25 ml) and saturated sodium bicarbonate solution (25 ml) and the insoluble solid was filtered and washed with water and ethyl acetate. The aqueous layer of the filtrate was extracted twice with dichloromethane and the combined organic extracts evaporated. The residue was combined with the ethyl acetate-insoluble material and treated with boiling ethanol (40 ml), unsoluble material being removed by filtration. Evaportion of the filtrate gave 2-n-propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol (0.7 g) as a solid NMR (d6DMSO) δ 8.84-8.68(1H,m), 8.18(2H,d), 6.82(2H,m), 6.7(3H,m), 4.1(1H,m), 3.42(4H,t), 3.17(3H,s), 3.05(4H,t), 2.48(DMSO), 1.55(2H,m), 0.89(3H,t).

Workup

  1. customwas hydrogenated at room temperature
  2. customCatalyst was removed by filtration through diatomaceous earth
  3. customthe filtrate evaporated
  4. customThe residue was triturated with a mixture of ethyl acetate (25 ml) and saturated sodium bicarbonate solution (25 ml)
  5. filtrationthe insoluble solid was filtered
  6. washwashed with water and ethyl acetate
  7. extractionThe aqueous layer of the filtrate was extracted twice with dichloromethane
  8. customthe combined organic extracts evaporated
  9. additiontreated with boiling ethanol (40 ml), unsoluble material
  10. custombeing removed by filtration

Sources & evidence

ORD record
ord-372ee0766f514314a4177039bddb9fe0
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Reaction notes

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